Re; What Rollo said!
Here is what Rollo Tomassi told me about this situation and which I think makes very good sense;
"One other thing you need to unlearn is this stupid social dogma that says a 44 y.o. guy 'shouldn't' get after a 25 y.o. woman. I can see from your post here that this is something you've internalized over the years as well. Push that out of your head now. The only people who would give you a sideways glance for being with a 25 y.o. are unmarried or divorced women in their mid 30's to early 40's who help perpetuate the myth that older men ought to date women their own age (like them for instance) and reward their bad life decisions up to this stage in their lives by "doing the right thing" and providing them with the security they seek rather than a hot piece of ass. Women in their 20's dont complain about the interests of older men, it's thirtysomething women faced with fading looks, unable to get the attention they used to when they were in their 20's who'll whine about how 'immature' men are for wanting 'trophy wives' half their age. It's just this psychology of entitlement that pervasively shames men for their "fragile egos" in an effort to get the provisioning that an older man can provide them when faced with competition from far more physically superior (and younger) women.
Interstingly enough there's no equitable shame when the genders are reversed in cases such as Demi Moore and Ashton Kutcher. None at all, in fact it's encouraged - you GO girl.
So unlearn this. Single at 44 and you damn near closed with a 25 y.o. woman? Why on planet earth would you not? Scrub this self-defeating feminized shame out of your brain today. You've subscribed to it to the point where it's hindered a personal decision for you with no peers to incriminate you so I can categorically say you've internalized this sh!t. Break this stupid mental schema. You are the PRIZE and no woman is entitled to anything you are capable of providing them. So if a 25 y.o. has caught your eye enough to flirt with her she's the fortunate one who'll get what you have to offer, not bitter 30-40 year olds. You're not going to marry her, you're only going to give her the flattering attentions of 44 y.o. prince. Now go get her, or find another one your even more hot for."
So my advice is ask her out NOW..., don't wait another second!
